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Mechanism of the formation of 1,2,4-thiadiazoles by condensation of aromatic thioamides and of N-substituted thioureas

✍ Scribed by Luciano Forlani; Andrea Lugli; Carta Boga; Anna Bonamartini Corradi; Paolo Sgarabotto

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 507 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370110

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✦ Synopsis

Abstract

The condensation reaction of thiobenzamide, (as well as thionicotinamide and isothionicotinamide) in the presence of dimethyl sulfoxide and of an acid, affords 3,5‐diphenyl‐1,2,4‐thiadiazole. Under the same experimental conditions, N‐substituted thioureas are also condensed to 1,2,4‐thiadiazole derivatives; their structure is ascertained by spectroscopic properties and by X‐ray diffraction. Some information on the mechanism of thiadiazoles formation from both starting classes of compounds, thiobenzamides and N‐substituted thiourea, is collected and discussed.

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